Dick Portillo, founder of the billion-dollar Portillo's hot dog chain, sold his company in 2014 but regrets it. He later bought back some locations and built a new real estate empire. Starting with $1,100, he created a highly successful restaurant chain known for its unique Chicago-style food and efficient operations. After selling, he invested in diverse ventures, including apartments, industrial properties, and other businesses. Though he enjoys his current life less, he's immensely wealthy, boasting a billion-dollar net worth and impressive real estate holdings across the US.

Prepared by Christopher Adams and reviewed by editorial team.